Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene

✍ Scribed by Ramón Badorrey; Carlos Cativiela; María D Díaz-de-Villegas; JoséA Gálvez

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 767 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00377-4

✦ Synopsis

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective tandem Mannich-Michael reaction with Danishefsky's diene in the presence of Lewis acids. The temperature, catalyst and solvent dependence of the product ratio is described. Under zinc iodide-catalysed conditions in acetonitrile at -20 °C, double stereodifferentiation using (R)-2,3-di-O-benzylglyceraldehyde (S)-N-a-(methylbenzyl)imine as starting material was successful and the reaction occurred with good yield and complete diastereoselectivity.